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The opinions expressed herein are the author's alone and have not been influenced by WebMD.
People who decide to include anal play in their sexual repertoire can approach it with several different attitudes and expectations. It's important to spend a little time finding out what your partner wants and, most importantly, doesn't want. Don't just plunge ahead assuming that you already understand. Anal sex is not the same thing for everybody.
Many people who don't discuss the parameters of their anal play beforehand find that their first experiment is their last one, usually because someone's expectations weren't met. There is a way to avoid such frustrations and difficulties. When first experimenting with anal play, let the receiver completely control the depth of insertion, the speed of movements and the duration of the activity. It's perfectly fine if your first experience lasts only a few seconds. If it's enjoyable, then subsequent explorations can take more time and include more activities.
To make anal sex play enjoyable and healthy, keep these tips in mind: Because no lubrication is produced by the anus, a lubricant should definitely be used to help the insertion of anything -- finger, penis or sex toy. Water-based lubricants are fine. Some of these can be purchased at drugstores or at a store that carries sensual accessories. Other more greasy lubricants are preferred by some who intend to spend a longer time at anal play.
One very important health precaution: Don't switch from anal intercourse or anal finger play to any vaginal contact without very thorough washing of the body part that contacted the anal area. This kind of contact can lead to persistent and uncomfortable vaginal infections, since anal bacteria find the vagina a very hospitable environment. Also keep in mind that a male inserting partner should urinate after anal intercourse to flush out his urethra.
To avoid transferring bacteria, use a condom or a finger covering called a "finger cot." Peel them off before having vaginal contact. If you remove these carefully, without touching the outside of the condom or cot, washing is not necessary. But note that if you use a greasy lubricant such as petroleum jelly you will greatly reduce the protection afforded by condoms, since the mineral oil will deteriorate latex.
If you want to have anal intercourse (or vaginal intercourse, for that matter) without a condom, you need to be completely sure about the health of your partner's genital tract. If you are certain that you are in a monogamous relationship and both partners have tested negative for chlamydia, human papilloma virus, trichomonas, syphilis, gonorrhea, gardnerella, herpes, and HIV (the virus that causes AIDS), you can opt not to use a condom.
Most people who are in the receiver role usually appreciate gentle, unhurried, and lubricated massaging of the area externally before any insertion is attempted. This usually will help to relax the anal sphincter and make insertion easier and potentially more pleasurable. People who have hemorrhoids can be receptive in anal play if they are not experiencing inflammation, bleeding or pain in that area. Explore the insertion of fingers first if hemorrhoids are present.
Anal sex play is likely to be more acceptable if the receiver has had a bowel movement sometime during the several hours preceding sexual contact. Washing in a bath or using a bidet will cleanse the outside area. Some people use a water enema for additional cleansing, but many do not.For additional information on this topic, I recommend Anal Pleasure and Health: A Guide for Men and Women by Jack Morin.

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